Velvet Theater Night

Sep 22 2025

Afternoon Boutique

Sep 20 2025

Rooftop Cocktails

Sep 20 2025

Speakeasy Soiree

Sep 20 2025

Speakeasy Soiree

Sep 20 2025

Gallery Opening

Sep 20 2025

Dinner With Friends

Sep 19 2025

Sep 10 2025

Dinner With Friends

Sep 19 2025

Rooftop Reflection

Sep 18 2025

Put together some cool looks to see Disclosure in San Diego. I want something street style that will look cool at a concert - San Diego Streetwear

Sep 18 2025

Michigan Avenue Amble

Sep 18 2025

River North Review

Sep 18 2025

Sunset Soir%C3%A9e

Sep 16 2025

Moonlit Rooftop

Sep 16 2025

Gallery Opening

Sep 15 2025

morning cafe

Sep 15 2025

Downtown Exhibition

Sep 13 2025

Edgy Supper Club

Sep 13 2025

Rainy Day Bookstore

Sep 13 2025

Evening Networking

Sep 12 2025

Transitional Workday

Sep 12 2025

Creative Office Showcase

Sep 12 2025

River North Supper

Sep 12 2025

Evening Bistro Dinner

Sep 11 2025

Evening Bistro Dinner

Sep 11 2025

Evening Bistro Dinner

Sep 11 2025

Gallery Stroll

Sep 11 2025

New Accounts

Sep 11 2025

New Accounts

Sep 11 2025

Gabby's Unveiling

Sep 10 2025

Gabby's Unveiling

Sep 10 2025

Gabby's Soho Showcase

Sep 10 2025

Outfit for shopping in west loop tomorrow mid day, with warm layers. Something simple to make it easy for me to try on clothes, but still trendy and interesting - Layered Shopper

Sep 07 2025

Theater District

Sep 06 2025

Cool Weather Meeting

Sep 06 2025

Cool Weather Meeting

Sep 06 2025

Autumn Evening Soiree

Sep 06 2025

Curated Showroom

Sep 06 2025

Curated Showroom

Sep 06 2025

Curated Showroom

Sep 06 2025

Late Night Lounge

Sep 06 2025

Late Night Lounge

Sep 06 2025

Gallery District Evening

Sep 05 2025

Gabby's Brand Launch

Sep 03 2025

City Loft Gathering

Sep 03 2025

Velvet Underground

Sep 02 2025

Evening Rooftop Views

Sep 02 2025

New City Soiree

Sep 01 2025

Gabby's Midnight

Sep 01 2025

Gabby's Pop-Up Exhibit

Sep 01 2025

Street Style Hunt

Sep 01 2025

City Loft Gathering

Aug 31 2025

City Loft Gathering

Aug 31 2025

Market Morning

Aug 31 2025

Neon Nights

Aug 31 2025

Gabby's Client Connect

Aug 30 2025

Gabby's Client Connect

Aug 30 2025

Techno Pulse

Aug 30 2025

Cool outfit for work with a pop of color - Artistic Office

Aug 27 2025

Cool outfit for work with a pop of color - Artistic Office

Aug 27 2025

dressy

Aug 26 2025

casual

Aug 26 2025

dressy- Something with different shoes and accessories and without an outerwear layer

Aug 26 2025

Twilight Speakeasy

Aug 26 2025

Cool transitional work outfit for cool weather - Urban Executive

Aug 25 2025

Gallery Opening

Aug 25 2025

Rooftop Views

Aug 21 2025

Fieldside Friends

Aug 20 2025

Downtown Brunch

Aug 17 2025

Gabby's Elevated Hour

Aug 16 2025

Humid Night Out

Aug 16 2025

Humid Night Out

Aug 16 2025

Curated Corner

Aug 15 2025

Golden Hour

Aug 15 2025

Jul 31 2025

Aug 01 2025

Aug 02 2025

Aug 03 2025

Aug 06 2025

Aug 08 2025

Downtown Bistro

Aug 14 2025

Gallery Gala

Aug 14 2025

Aug 14 2025

Aug 13 2025

Aug 12 2025